Every year, nearly half a million U.S. teachers either move or leave the profession. It is estimated teacher retention issues cost the United States up to $2.2 billion annually (Alliance for Excellent Education, 2014). This phenomenological study focused on rural superintendent perspectives on the impact principal leadership and teacher mentoring have on teacher retention. Limited research has been conducted on superintendent perspectives on teacher retention. The majority of research on teacher retention has involved the perspective of teachers. This qualitative study was conducted using semi-structured interviews with eight rural superintendents from REAP (Rural Education Achievement Program) eligible schools. Findings were analyzed in multiple rounds of coding and included themes consisting of financial considerations, supportive culture, principal longevity, communication, trust, program length, paperwork, and mentors. Recommendations are given from a critical analysis on the findings in this study. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]